A novel baker's yeast catalysed hydride reduction of an epoxide moiety

RM Horak, RA Learmonth, VJ Maharaj

Index: Horak, R. Marthinus; Learmonth, Robin A.; Maharaj, Vinesh J. Tetrahedron Letters, 1995 , vol. 36, # 9 p. 1541 - 1544

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Citation Number: 4

Abstract

The preparation of 2-[2H]-1-(p-nitrophenyl)-1, 2-epoxyheptan-3-one and its subsequent reduction by baker's yeast to the 2, 3-diol is described. The mechanism of the reduction of the epoxide was determined using the β-2H isotope shift in13C nmr and mass spectroscopy and appears to be due to a novel enzyme catalysed hydride transfer from cofactors such as NADH or NADPH.